Azo dyestuffs and material dyed therewith



Patented Dec. 23,1930

uni-TED sra'riszs' ounce KARI; 'rnrnsson FRANKFORT-O N-rRR-MAIN-noonsr. GERMANY, AssIoNoR r enn- ERAL Animus WORKS, "1120., oRNEW YORK, 11. Y., A CORPORATION or DELAWARE "li zo nYRsrurRs AND MATERIAL DYED THR EWITH Remaining. Application filed August 26, 1929, Serial No. 388,628, and in Germany September 18, 1928.

My present-invention relates to azo dye-f stuffs and material dyed therewith.

I have found; that new valuable azo dye stuffs, which can be produced in substance as well as on thefiber, arev obtained" by coupling the diazo compoundof a 5-h'alogen-2-j amino-l-benzoic acid alkyl-esterwith a naphthylamideot the 2.3-hydroxynaphthoic acid.

. These dyestuffs which are characterized'by the following general formula:

wherein R stands for a halogen atom,

R for an alkyl group and e R for a naphthyl group the hydrogen atoms of which may be substituted or not,

are distinguished by the particular purity of their tints and their good tastness properties, especially by their good fastness to light.

The following examples serve to illustrate my invention but they are not intended to limit it thereto:

Dyeing prescription for Examples 13 50 grams-of boiled cotton are treated for half an hour in the grounding liquor, well hydro-extracted and'dyed for half an hour in the dye bath. The material is then rinsed cold and hot, soaped at boiling temperature, rinsed and dried. I I

1. (a) Grounding liquor of 2.3-hydroxynaphthoic acid-beta-naphthyl-amide,

4 com. of Turkey red oil of 50 per cent strength and 6 com. of caustic soda solution of 34 Be. are dissolved in 200 com. of distilled. water heated to boiling temperature, cooled clown to 50 C., mixed with 2 ccin. of formaldehyde of 30 per cent strength and the t whole is then made up with water to A particularly vivid scarlet-red of very' good fastness tolight, washingand kier-boiL' ing is obtained.

2. (a) Grounding liquor 4.5 g. of hyrorynaphthoic acid alpha naphthyl- 9 com. of Turkey red oil of 50 per cent strength and 13.5 ccm. of caustic soda solution of 34" Be. are dissolved in 200 com. of distilled water heated to boiling temperature, the solution is cooled down to 50C., mixed with formaldehyde of 30 per cent strength and the whole is made up with'water to v (b) Dye bath 4.5 com. of 1 liter.

A red dyeing of very good fastness properties is obtained.

3. (a) Grounding liquor of Turkey red oil of 50 per cent strength and of caustic soda solution of 34 B6. are dissolved CDH N) in 200 ccm. of distilled water, heated to boiling temperature, the solution iscocleddown to 50 C., 2 com. of formaldehyde of 30 per cent strength are added and the whole is made up with water to 1 liter.

(b) Dye bath 2.3 g. of 5-bromo-2-an1ino-benzoic acid-methyl ester are diazotized in the cold with r 2.8 ccm. of hydrochloric acid of 22 Be. and

0.75 g. of sodium nitrite dissolved in water. The mass is rendered neutral to Congo paper by means of about 2 g. of sodium acetate,

25-50 g. of sodium chloride are added and the whole is 1 H made up with water to y There is obtained a particularly vivid scarlet-red coloration of very good fastness prop erties, which has a somewhat more bluish shade than that prepared according to Example 1.

' Ewam-ple 4 20 parts by weight of 5-chloro-2-aminobenzoic acid-methyl ester are diazotized according to known methods by means of h 'drochloric acid and sodium nitrite, The d iazo solution which is filtered if requisite, is coupled with a caustic'alkaline aqueous solution of 31.3-parts by weight of 2.3-hydr0xynaphthoic acid-beta-naphthyl-amide at a temof 2.3-hydroxyna1ih thoic acid-beta-uaphthyl-amide,

perature offrom C to O. The d yethe ethyl-, propyland butyl esters there are ebtained dyestuffs and dyeings of equal prop- A R fora naphthyl groupjthe hydrogeni stuff precipitates at .once' inthe form of bright scarlet-red flakes After filtration the dyestuif is washed withwaternand further brought into the form of a pastefor instance for the preparation oflacquers. a I o By using other esters such for instance as crtie's, t

I claim: 1. As new products, the

R 'stands for a halogen atom, j R2 for an alkyl group and atoms of-which may be 'substitutedor V not, I

dyeingred' tint sand-being distinguished by 7 their good fastness properties, particularly by their good fastne s's to lightf 2. As new-products,-;the compounds ofthe V Vjfollowing general formula: a0

Y or i on "oo.NH.R|' wherein I i R stands for a halogen atom, R for an alkyl group and ,r l eund f the following general formula:

claimed in cl'aim'5.

R stands for a halogenatom dyeing red tints and being distinguished by their good fastness properties, particularly by their good fastness to light. 5L Asa new product, the compound of the following formula: r f

1 .its good fastness to light. i

6. Materialdyed with thedyestufis claimed inc laim 1.v V v r I o 7:: Material dyed withthedyestuifs claimed in1claim2. Y

so i

8. 'Material dyed with the v in claim 3. F [9. Material incl aiml. :77 t.

10. Material dyed with "the In testimony whereof; I fafliximy signature. KARL THIESS.

R for an alpha-tor beta-naphthylgrou p,

4b dyeing red tints andbeing distinguished by theirgood fastness properties, particularly 1 their good. fastness to light. I

3. As new products, the compounds of the following general formula wherein A j R stands for a halogen atom and t R for an alpha-or beta-naphthyl. group,

dyeing red tints and being distinguished by their good fastness properties, particularly by their good fastness to light.

4. As new products, the compounds of the following general formula:

wherein 

